Category: amides-buliding-blocks

Electric Literature of 406233-31-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 406233-31-6 as follows.

Into a1 OO-mL round-bottom flask, was placed 4-fluoro-3-nitrobenzene- 1- sulfonamide (1.43 g, 0.007 mmol, 1 equiv), i-[(25)-i,4-dioxan-2-yljmethanamine hydrochloride (1 g, 6.5 10 mmol, 1 equiv), THF (30 mL), Cs2CO3 (8.48 g, 0.026 mmol, 4 equiv). The resulting solution was stirred overnight at 50C in an oil bath. The solids were collected by filtration. The solid was dried in an oven under reduced pressure. This resulted in 1.82 g (88.10%) of 4-([[(25)-i,4-dioxan-2- ylj methylj amino)-3 -nitrobenzene- 1- sulfonamide as a yellow solid. LC-MS: (ES, m/z):M+i=318, R,T= 0.741 mm. ee=99%, [aj = -17.4 (C= 0.102 g in 100 ml DMSO, T=27C).

According to the analysis of related databases, 406233-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
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915087-25-1, The chemical industry reduces the impact on the environment during synthesis 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

Compound I (100 g, 0.594 mol) is suspended in 300 mL of dioxane. TEA (250 mL, 3.59 mol) is added by pouring in a thin stream. The system is placed under nitrogen, and heated to 60C. A solution of intermediate II (160 g, 0.90 mol) in 150 mL of dioxane is prepared separately. The solution of compound II is added to the suspension in the reactor and left to react for about 20 hours. The mixture is cooled to l5C and filtered through a Biichner funnel, washing the cake twice with 100 mL of dioxane each time. The resulting product is suspended in 1200 mL of water, 1M HC1 is added until a pH < 3 is reached, and the resulting suspension is then filtered through a Buchner funnel, washing the cake twice with 200 mL of water each time. The crystal thus isolated is dried under vacuum at the temperature of 60C, providing intermediate III in a 76% yield (120 g, 45.1 mmol) and 99.6% HPLC purity. NMR (300MHz, CDCh) d 15.3 (m, 4H), 2.58 (t, br, 2H), 2.73 (s, 3H), 6.00 (m, 1 H), 6.22 (s, 1 H), 7.17 (s, 1H), 7.46 (s, 1H), 7.65 (d, 1H), 12.63 (m, 1H). The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life. Reference:
Patent; OLON S.P.A.; GRANDE, Valentina; FERRETTI, Gabriele; NOVO, Barbara; (0 pag.)WO2019/229625; (2019); A1;,
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Synthetic Route of 144-80-9, A common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, molecular formula is C8H10N2O3S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

0.6 g (0.0028 mol) of sulfacetamide was dissolved in 20 mL of N,N-dimethylformamide.then,1.0 g (0.0316 mol) ofloxacin and 1.3 g (0.0063 mol) of dicyclohexylcarbodiimide were added.Heating to 80 C for heating,And stirring for 15 hours,Obtaining an initial ofloxacin-sulfacetamide hybrid drug reaction solution,among them,In order to understand the progress of the reaction in time,The reaction was followed by a thin layer chromatography silica gel plate.In the process,Ofloxacin gradually dissolves,The solution turns orange-red;The initial ofloxacin-sulfacetamide hybrid drug reaction solution is subjected to impurity removal treatment to obtain a purified substance of ofloxacin-sulfaacetic acid hybrid drug.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Wuhan Institute of Technology; Zhu Hong; Li Shuang; Zhang Huan; Ding Jiao; Li Li; Zeng Xiangcong; Li Xue; (6 pag.)CN109438473; (2019); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1172623-95-8, name is tert-Butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1172623-95-8

Under N2 protection, 2,3,5-trifluorobromobenzene (42.2 g, 200 mmol) was dissolved in dry toluene (50 ml),cooled to -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(100 ml, 2.2 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (25.6 g, 100 mmol)was dissolved in dry tetrahydrofuran (250 ml), and added dropwise to the reaction solution while the temperature wasmaintained at -10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4hours. The temperature was lowered to about -10C, and a saturated ammonium chloride solution (100 ml) was added dropwise, followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allowsettling and partitioning. The aqueous phase was extracted with methyl t-butyl ether (150 ml32). The organic phaseswere combined, washed with a saturated sodium chloride solution (100 ml32), dried by addition of anhydrous sodiumsulfate thereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) =50:1 to 8:1), to obtain a white solid 3A (27 g, yield 82.6%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1172623-95-8.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

A mixture of 2-(4-fluoropiperidin-l-yl)acetic acid(239 mg, 1.48 mmol), HATU (619 mg, l.63mmol) and DIPEA (524 mg, 4.44 mmol) in DCM (10 mL) and DMF(lOmL) was stirred at room temperature for 0.5 h. Then tert- butyl 4-aminophenethylcarbamate (350 mg, 1.48 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (400 mg, 71.3% yield). ‘H NMR (500 MHz, DMSO- d6) d: 10.38 (s, 1H), 7.50 (d, J= 8.3 Hz, 2H), 7.18 (t, J= 8.5 Hz, 2H), 6.87 (d, J= 5.5 Hz, 1H), (0881) 4.92 (d, J= 52.6 Hz, 1H), 3.95 (dd, J= 34.1, 9.3 Hz, 1H), 3.11 (dd, J= 13.9, 6.5 Hz, 5H), 2.81 (d, .7= 79.7 Hz, 1H), 2.65 (t, J= 7.4 Hz, 2H), 2.20 – 1.99 (m, 4H), 1.91 (s, 1H), 1.36 (s, 10H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 94838-59-2.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(4-Fluorophenyl)-N,N-dimethylacrylamide

General procedure: The dihydro-6H-quinolin-5-one (3a-v) were synthesized based on aliterature method as following: aryl and heteroaryl methylketones(1a-k, 5.23 mmol) were treated with dimethylformamide-dimethylacetal(DMF-DMA) (20.92 mmol) in refluxing xylene for 7 h to form beta-enaminones (2a-k), and reacted with cyclohexane-1,3-dione/5,5-dimethylcyclohexane-1,3-dione (0.16 g, 1.2 mmol) ammonium acetate(2.0 mmol) in 2-propanol (5 mL) were added CeCl3·7H2O (0.2 mmol),NaI (0.2 mmol) and refluxed for 4 h (monitored by TLC). The reactionmixture was cooled to room temperature; a solid precipitate was filteredand washed with cold 2-propanol. The combined solvent wasevaporated, and the crude residue obtained was subjected to columnchromatography (hexane: ethyl acetate) to obtain dihydro-6H-quinolin-5-one derivatives (3a-v) as solids in very good yields.

According to the analysis of related databases, 75175-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kantevari, Srinivas; Krishna, Vagolu Siva; Marvadi, Sandeep kumar; Sridhar, Balasubramanian; Srilakshmi Reshma, Rudraraju; Sriram, Dharmarajan; Surineni, Goverdhan; Bioorganic Chemistry; vol. 96; (2020);,
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Reference of 6228-73-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6228-73-5, name is Cyclopropanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows.

Cyclopropanecarboxamide (58.7g, 690 mmol) in 1,4-Dioxane (1600 ml) was added 2-bromoacetyl bromide (59.9 ml, 690 mmol) at room temperature and stirred for 4h at 600C. The reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and carefully washed with satd. NaHCObeta, water then with brine solution, dried over Na2SO4 and concentrated to get N-(2- bromoacetyl) cyclopropanecarboxamide(138 g, 670 mmol, 97 % yield) as an off white solid. This material was used without purification. ESI-MS :m/z 208.0 (M+2H)+.

The chemical industry reduces the impact on the environment during synthesis Cyclopropanecarboxamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
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Synthetic Route of 1346674-23-4,Some common heterocyclic compound, 1346674-23-4, name is 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one, molecular formula is C12H16N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 128a 2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzaldehyde 128a A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one 103e (1.0 g, 4.90 mmol, 1.0 eq.), 2-bromo-6-chloro-4-fluorobenzaldehyde (2.76 g, 9.8 mmol, 2.0 eq.), Pd2(dba)3 (224 mg, 0.24 mmol, 0.050 eq.), Xantphos (283 mg, 0.49 mmol, 0.10 eq.), potassium acetate (1.44 g, 14.7 mmol, 3.0 eq.), and 1,4-dioxane (50 mL). The system was evacuated and refilled with N2. The reaction mixture was heated at 80 C. for 5 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified on silica-gel column eluting with 80:1 dichloromethane/methanol to afford 128a as a yellow solid (992 mg, 50%). MS: [M+H]+ 405.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7,7-Dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Young, Wendy B.; US2013/116245; (2013); A1;,
Amide – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

A solution of potassium tert-butoxide (1? 5eq) was added to a solution of (1-hydroxymethylcyclopropyl) -tert-butoxycarbonylamino in tetrahydrofuran [THF] at room temperature. After stirring for 30 min, 4-fluoro-2-isopropyl Oxy-1-nitrobenzene (1.3 eq) and heated to 50 C overnight. After completion of the reaction, the reaction solution was cooled, poured into water and extracted three times with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and then poured onto the column. PE [petroleum ether]: EA [ethyl acetate] Volume ratio) = 5: 1 to obtain compound 4-3.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Geng Meiyu; Song Zilan; Ai Qing; Liu Zhiqing; Chen Yi; Peng Xia; Ding Jian; (29 pag.)CN107216319; (2017); A;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1314538-55-0, Product Details of 1314538-55-0

To a N2 purged flask containing O-Silyl imidazole 8a or 8b (2.0 mmol, 1.0 equiv.), Pd(OAc)2 (0.2 mmol, 0.1 eq.), XPhos (0.2 mmol, 0.1 eq.), tert- butoxycarbonyl)amino)methyl) trifluoroborate (2.2 mmol, 1.1 eq.) and K2C03 (6 mmol, 3.0 equiv.) was added 6 mL degassed toluene and 1.5 mL degassed water. The reaction was then heated to 75 C for 18 hours. Upon completion, the reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was then collected and dried over Na2S04 followed by filtration and concentration via rotary-evaporation. The crude material was then purified using silica gel column chromatography (2:1 Ethyl Acetate: Hexanes to 10:1 Ethyl Acetate: Hexanes) to yield the Boc- protected amino-product as a white solid (50-60% yield)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; HERGENROTHER, Paul J.; GEDDES, Emily Jane; DROWN, Bryon Shane; MOTIKA, Stephen E.; PARKER, Erika Nicole; (141 pag.)WO2019/177975; (2019); A1;,
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Amide – an overview | ScienceDirect Topics